## United States Court of App eals

F O R T H E E I G H T H C I R C U I T

__ __ __ __ __ _
No. 1 0- 33 35

__ __ __ __ __ _ Uni te d S ta te s o f Am eri ca, *

* App el le e, *

* App eal fro m

th e Uni te d S ta te s

v. * Dis tri ct Co ur t fo r th e
* W es te rn Dis tri ct of M is so ur i. Bran do n L. Ben ne tt , *

* App el la nt

. *

__ __ __ __ __ _
Su bm it te d: Ju ne 17 , 20 11 Fi le d: Octo be r 19 , 20 11

__ __ __ __ __ _ Befo re MUR PHY an d S MITH, Ci rcu it Ju dg es , and SCHREIER, Dis tri ct Ju dg e. 1

__ __ __ __ __ _
SMI TH, Circ ui t J ud ge

.

Bran do n Ben ne tt pl ead ed gu il ty to di st rib ut i n g an d co ns pi rin g to di st rib ut e Ben zy lp ip eraz in e (BZP) in vi ol at io n of fed eral la w. At se nt en ci ng , Ben ne tt ob jecte d

to th e di st ric t co ur t's co nc lu si on th at BZP was su ffi ci en tl y eq ui va le nt to 2
Met hylen ed io xym et ha m

ph et am in e (MDM A)—t he ch em ic al na m e fo r th e dr ug

The Hon or ab le Karen E. Sc hr ei er, Ch ie f Ju dg e, Uni te d S ta te s Di st ric t Co ur t 1 fo r th e Dis tri ct of S ou th Dako ta , si tt in g b y de si gn at io n.

The Hon or ab le Greg Kay s, Uni te d St at es Dis tri ct Ju dg e fo r th e W es t e r n 2 Dis tri ct of M is so ur i.co m

m on ly cal le d "Ecs ta sy"—t o co m pu te Ben ne tt 's dr u g qu an ti ty un de r th e Sen te nc in g Gui de li ne s. Th e d is tri ct co ur t de ni ed Ben ne tt 's ob jecti on an d se nt en ced
Ben ne tt at th e bo tt om of th e ad vi so ry Gui de li ne s ran ge to 57 m on th s' im pr is on m en t. Ben ne tt ap pe al s an d, fo r th e rea so ns th at fol lo w, we affi rm

.

I. Bac kg ro un d
On Aug us t 11
, 20 08
, Ja ck so n Co un ty, Mi ss ou ri Dru g Task Fo rc e o ffi cers
pu rch as ed 50 ta bl et s of BZP fo r $4 00 fro m Ben ne tt th ro ug h a co nf id en ti al in fo rm an t. On Aug us t 21
, 20 08
, an un de rco ve r de te ct iv e pu rch as ed fiv e ta bl et s of BZP fo r $5 0 fro m Ben ne tt

. On Aug us t 29
, 20 08
, a se co nd de te ct iv e pu rch as ed 10 0 BZP ta bl et s fo r $7 75 . On Sep te m

be r 4, 2 00 8, au th or it ie s p ur ch as ed an ot he r 10 0 t ab le ts for $7 50

.

On Octo be r 29
, 20 08
, au th or it ie s arre st ed Ben ne tt aft er a fai l e d at te m pt to
pu rch as e an ot he r 10 0 BZP ta bl et s. Ben ne tt waiv ed hi s Mir an da rig ht s an d pr om pt ly

co nf es se d to se ll in g th e t a b l e t s an d pu rch as in g th em fro m hi s co de fen da nt , Ran dy
"Ro ll er Co as te r" Ro bi ns on

. Su bs eq ue n t l y, B en ne tt pl ead ed gu il ty to two co un ts of di st rib ut in g BZP, in vi ol at i o n of 21 U.S.C. §§ 84 1( a)(1 ) an d 84 1( b) (1 )(C) , a nd on e

co un t o f co ns pi rin g to di st rib ut e BZP, in vi ol at io n of 21 U.S.C. §§ 84 1( a)(1 ),
84 1( b) (1 )(C) an d 8 46

.

Befo re hi s se nt en ci ng he ar ing
, Be nne tt fi le d a se nte nc ing m em or an du m arg ui ng th at th e "s en te nc in g gu id el in es co nt ai n no refe ren ce to BZP at al l" an d th at , "[b ]ecaus e th e Sen te nc in g Co m m is si on ha s n ot st ud ie d B ZP, t he co ur t ha s no ba si s
to de fer to th e ad vi so ry gu id el in e ran ge as a reas on ab le se nt en ce." Ben ne tt at ta ch ed

to hi s se nt en ci ng m em or an du m a st ud y fro m th e Nati on al Dru g In te ll ig en ce Cen te r in di cat in g th at th e typic al do sa ge of BZP ran ge s fro m 20 to 20 0 m il li gr am s, an d th at "BZP is 10 to 20 ti m es le ss p o t e n t t h a n am ph et am in e." Ben ne tt al so ci te d a di st ric t

co ur t cas e fro m th e Mi dd le Dis tri ct of Alab am a in whi ch th e di st ric t jud ge co nc lu de d th at BZP was le ss po te nt th an Ecst as y an d va rie d do wnwar d on th at ba si s. Se e Uni te d
St at es v. Ros e , 72 2 F . Sup p. 2 d 1 28 6 (M .D. Ala. 20 10 ).

-2

-On May 25
, 20 10
, th e di st ric t cou rt co nt in ue d Ben ne tt 's se nt en ci ng to fu rth er

rev ie w Ben ne tt ' s ob

jecti on s to BZP an d MDMA's rel at ed ne ss

. In res po ns e, Uni te d
St at es Pr oba tio n au

tho red a se co nd ad de nd um to th e Pres en te nc e In ve st ig at io n Report (PSR ) in whi ch it cal cu la te d Ben ne tt 's ba se of fen se le ve l pu rs ua nt to U.S.S.G. §
2D1 .1, App li cat io n Not e 5. Tha t pr ov is io n di rect s th e se nt en ci ng co ur t to de te rm in e th e am ou nt , fo r se nt en ci ng pu rp os es , of a co nt ro ll ed su bs ta nc e ba se d on th e

mar i hu an a eq ui va le nc y of th e m os t cl os el y rel at ed co nt ro ll ed su bs ta nc e refe re n c e d in th e Gui de li n e s

. The PSR de te rm in ed th at BZP was m os t cl os el y rel at ed to MDMA/ Ecst a s y. A c c or di ng to th e dr ug eq ui va le nc y ta bl e, on e gr am of MDMA
eq ua ls 50 0 gr am s of m ari hu an a. App ro xi m at el y 33 0 gr am s of BZP was at tri bu te d to 3
B e n ne tt , whi ch is ro ug hl y eq ua l to 16 5 ki lo gr am s of m ari hu an a, y ie ld in g a b a s e of fen se lev el of 2 6.

O n O ct obe r 5, 20 10
, th e di st ric t co ur t reco nv en ed Ben ne tt 's se nt en ci ng he ar ing

. The co ur t o pe ne d t he he ari ng , st at in g:

THE COURT: And I be li ev e Mr. Mo ss ha s fil ed a s e n t e n c in g

m em or an du m on Aug us t 30 th
, 20 10
, as well

. And I wil l ad vi se th e—t he pa rti es a nd so th e
reco rd is cl ea r , I ha ve re vi ewe d al l th os e do cu men ts

. I ha ve rev ie wed —I'v e rece iv ed so m e

m or e—a no th er le tt er, at le as t o n e ot he r le tt er in

su pp or t of Mr. Ben ne tt

. And I ha ve rev ie wed al l

The Sen te nc in g Gu id el in es pro vi de , in pe rti ne nt pa rt, t ha t " [i]n t he cas e o f a 3

co nt ro ll ed su bs ta nc e th at is no t sp eci fic al ly refe ren c e d in [th e dr ug -q ua nt it y gu id el in e], de te rm in e th e ba se of fen se le ve l us in g th e m ari hu an a eq ui va le nc y of th e

m ost cl osel y rel at ed co nt ro ll ed su bs ta nc e refe ren ced in [th e dr ug- qua nti ty gui de lin e]

. " U.S.S.G. § 2 D1.1 , cm

t. 5

. -3

-th e le tt ers in th is fil e fro m hi s p a r e n ts , si st ers , an d ot he r p e o p le
, an d I ha ve re vi ewe d th e pr es en te nc e in ves ti

ga ti on rep or t a ga in

. (Em ph as es ad de d.)

The di st ric t co ur t it em iz ed each of th e § 35 53 (a) fact or s an d an al y zed Ben ne tt 's
of fen se an d c i rcu m st an ces in rel at io n to th os e fact or s. Befo re an no un ci ng th e

se nt en ce, t he di st ric t co ur t s ai d:

THE COURT: So I'v e—I 'v e t h o u g h t a b o u t t h i s a l o n g ti m e.

Mr.— Mr. Mo ss ha s mad e so m e pr et ty go od arg um en ts du rin g th e co ur se of th is c a s e th at req ui red m e to do so m e res earc h an d req ui red th e pr ob at io n pe op le to —t o lo ok at th is dr u g th at we' r e de al in g wit h th is
, th is BZP. W hi le it m ay
no t be in th e se nt en ci ng gu id el in es , it is il le ga l. It do es affe ct th e co m

m un it y

. It do es hu rt ch il dr en

. It d o e s hu rt pe op le in ou r co m m un it y

. So wit h th at sa id
, I—I th in k I fas hi on ed a se nt en ce th at I ho pe is co ns is te nt wit h ou r—wi th th e gu id el in es , an d a ls o c on si st en t wi th th e g oa ls of 3 55 3( a).

Co nc lu di ng BZP was su ffi ci en tl y rel at ed t o Ecst as y , th e di st ric t co ur t cal cu la te d Ben ne tt 's ad vi so ry Gui de li ne s ran ge at 57 to 71 m on th s' im pr i s o n men t. Ben ne tt req ue st ed a do wnwar d va ria nc e of 36 m on th s ba se d on th e la ck of BZP an d
Ecst as y rel at ed ne ss , bu t th e di st ric t co u rt se nt en ced Ben ne tt at th e bo tt om of th e ad vi so ry Gui de li ne s ra ng e to 57 m on th s' i m pr is on m en t.

II. Dis cu ss io n On ap pe al
, Ben ne tt m ai nt ai ns th at th e di st ric t co ur t co m m it te d pr ejud ic ia l
pr oc ed ur al erro r by fai li ng to co ns id er Ben ne tt 's ob jecti on s th at BZP is in su ffi ci en tl y

-4

-si m il ar to MDMA, in bo th po te nc y an d pr op ert ie s , t o jus ti fy th e us e of th e MDMA

qu an ti ty tab le s i n c al cu la ti ng th e Gui de li ne s ra ng e ap pl ic ab le to a BZP o ffen se

.

"In rev ie win g fo r pr oc ed ur al erro r, we rev ie w th e di st ric t co ur t's ap pl ic at io n of th e [G]uid el in es de no vo an d it s fact ua l fin di ng s fo r cl ear er r o r

. " Uni te d St at es v. Dixo n , —F.3 d—
, No. 10 -3 64 4, 20 11 W L 35 57 87 2, at *3 (8 th Ci r. Aug

. 1 5, 20 11 ) (ci ti ng Uni te d St at es v. Paz , 62 2 F.3 d 89 0, 89 1 (8 th Ci r. 20 10 )). Mo reo ve r, whe n th e de fen da nt do es no t ob

ject at se nt en ci ng to an a l l e ge d pr oc ed ur al de fect
, we rev ie w

on ly fo r pl ai n erro r. U

n i t e d St at es v. To wn se nd , 6 18 F.3 d 91 5, 91 8 (8 th Ci r. 20 10 ).
Howev er, be cau se a rev ie w of th e tra ns cri pt rev eal s th at Ben n e t t di d

co nt em po ran eo us ly ob

ject to th e di st ric t co ur t's ap pl ic at io n of th e § 35 53 (a) fact or s, pl ai n- erro r rev ie w do es no t ap pl y he re.

In rev ie win g a cri m in al de fen da nt 's se nt en ce, we "'m us t fir st en su re th at th e di st ric t co ur t co m

m it te d no si gn ifi can t pr oc ed ur al erro r.'" Uni te d St at es v. Feems te r , 57 2 F.3 d 45 5, 46 1 (8 th Ci r. 20 09 ) (en ba nc ) (q uo ti ng Gal l v. Uni te d St at es , 55 2 U.S. 3 8
, 51 (2 00 7) ). "'Pr oc ed ur al erro r' in cl ud es 'fai li ng to cal cu la te (o r im pr op e r l y cal cu la ti ng ) th e Gui de li ne s ran ge , tre at in g th e Gui de li ne s as m an da t o r y, f a il in g to

co ns id er th e § 35 53 (a

) fa ct or s , se le ct in g a se nt en ce ba se d on cl earl y erro ne ou s fact s,

or fa il in g to ad eq ua te l

y exp la in th e ch os en se nt en ce— in cl ud in g an ex pl an at io n fo r

an y de vi at io n fro m th e Gui de li ne s ran ge .'" Id

. (em ph as es ad de d) (q uo ti ng Gal l
, 55 2 U.S. a t 51 ). Here, Ben ne tt m a i n t a in s th at th e di st ric t co ur t pr oc ed ur al ly err ed whe n it (1 ) "i g n o r e d u nd is pu te d sc ie nt ifi c st ud ie s an d le ga l au th or it y th at de m on st rat ed
BZP is si gn ifi can tl y le ss se rio us , le ss ha rm fu l, an d le ss da ng ero us th an bo th MDMA

an d am ph et am in e"; an d (2 ) fai le d to ad eq ua te ly ex pl ai n it s reas on s fo r reject in g Ben ne tt 's ev id en ce an d a r g u men t co nc ern in g BZP's an d MDMA's la ck of

co m m on al it y . Bot h o f Ben ne tt 's a rg um en ts are m eri tl es s.

Co nc ern in g Ben n e t t ' s fir st po in t th at th e di st ric t co ur t who ll y "i gn or ed " hi s ob jecti on th at BZP an d MDMA la ck ed su ffi ci en t eq ui va le nc y , th e reco rd refl ect s th at th e di st ric t co ur t ap pr op ria te ly co ns id ered whe th e r t h e two dr ug s were su ffi ci en tl y

-5

-rel at ed

. The di st ric t co ur t co nf irmed at se nt en ci ng th at it ha d rev ie wed al l th e

ev id en ce th at Ben ne tt su bm it te d. The di st ric t co ur t st res se d th at it ha d "t ho ug ht ab ou t th is a lo ng ti m e" an d ack no wled ge d t ha t "M r. Mo ss ha [d ] m ad e so m e pr et ty go od
arg um en ts du rin g th e co ur se of th is cas e." Mo reo ve r, an d pe rh ap s m os t te ll in gl y , th e di st ric t co ur t, in res po ns e to Ben ne tt 's in it ia l se nt en ci ng m em or an du m , ac t u a l ly

co nt in ue d Ben ne tt 's se nt en ci ng fo r ov er fiv e m on th s an d or de red a se co nd ad de nd um
to th e PSR fo r th e sp eci fic pu rp os e of ad dr es si ng Ben ne tt 's BZP arg um en t. Thu s, th e

reco rd refu te s Ben ne tt 's co nt en ti on th at t h e d is tri ct co ur t de cl in ed to ev en co ns id er hi s B ZP ob

jecti on

.

Add it io na l l y, th e di st ric t co ur t ad eq ua te ly ex pl ai ne d why BZP an d MDMA

w ere su ffi ci en tl y rel at ed

. Alt ho ug h "'[w]e do no t req ui re di st ric t co ur ts t o

m e c h a n i c a l ly reci te th e § 35 53 (a) fact or s whe n it is cl ear th e fact or s were pr op erl y

co ns id ered ,'" Dixo n , 20 11 W L 35 57 87 2, at *3 (q uo ti ng Uni te d St at es v. Bro wn , 62 7 F.3 d 10 68
, 10 73 (8 th Ci r. 20 10 )), a rev ie w of th e se nt en ci ng -h eari ng t r a n sc rip t

rev eal s th at th e di st ric t co ur t reci te d al l of th e § 35 53 (a) fact or s an d ga ve it s rat io na le fo r a Gui de li ne s se nt en ce in Ben ne tt 's cas e ba se d on each fact o r ' s r e s p ect iv e go al

. Id eal l y, a di st ric t co ur t sh ou ld craf t it s ex pl an at io n of dr ug eq ui va le nc y in th e la ng ua ge em

pl oyed by th e Gui de li ne s. Sp eci fic al ly, U.S.S.G. § 2D1 .1(c ) se ts ou t th e Gui de li ne s' "Dru g Qua nt it y Tab le ." App li cat io n Not e 5 to th at Gui de li ne s se ct io n
go ve rn s " Ana lo gu es an d C on tro ll ed Su bs ta nc es Not Refe ren ced in th is Gui de li ne ,"

an d pr ov id es th at , "[i ]n de te rm in in g th e m os t cl os el y rel at ed co nt ro ll ed su bs ta nc e" fo r th e p ur po se s o f § 2 D1.1 , th e d is tri ct co ur t

sh al l, t o t he ex te nt pra ct ic ab le , con si de r th e fo ll owi ng :
(A) W he th er th e co nt ro ll e d s u bs ta nc e no t refe ren ced in th is gu id el in e ha s a ch em ic al st ru ct ur e th at is su bs ta nt ia ll y si m il ar to

a co nt ro ll ed su bs ta nc e ref eren ced in th is gu id el in e.
(B) W he th er th e co nt ro ll ed su bs ta nc e no t r e f eren ced in th is gu id el in e ha s a st im

ul an t, de pr es sa nt , or ha ll uc in og en ic effe ct on th e cen tra l ne rv ou s syste m th at is su bs ta nt ia ll y si m il a r t o th e -6

-st im ul an t, de pr es sa nt , or ha ll uc in og en ic effe ct on t he cen tra l

ne rv ou s syste m of a co nt ro ll ed su bs ta nc e r e f eren ced in th is gu id el in e.
(C ) Wh e t he r a le ss er or gr eat er qu an ti ty of th e co nt ro ll ed

su bs ta nc e no t refe ren ced in th is gu id el in e is ne ed ed to pr od uc e a
su bs ta nt ia ll y si m il ar e f

f e c t on th e cen tra l ne rv ou s syste m as a
co nt ro ll ed su bs ta nc e ref

eren ced in th is gu id el in e.

Alt ho ug h th e di st ric t cou rt di d no t exp la in in th es e p reci se ter m s its co nc lu si on th at BZP an d MD M A w e r e su ffi ci en tl y eq ui va le nt fo r Gui de li ne s pu rp os es , th e reco rd sh ows th at th e di st ric t co ur t co ns id ered th es e an d o th er ch arac te ris ti cs of t he dru gs

. Fo r in st an ce, at t h e s e n te nc in g he ari ng , t he di st ric t co ur t co m m en te d th at Ben ne tt 's
arg um en ts

re qu ir ed [t he co ur t

] t o do so me re se ar ch an d req ui red th e pr ob at io n pe op le to —t o l o o k a t t h i s dr ug th at we'r e de al in g wi th th is

, th is BZP

. W hi le it m ay no t be in th e se nt en ci n g g u i d e li ne s, it is il le ga l. It do es affe ct th e co m

m un it y

. It do es hu rt ch il dr en

. It do es hu rt pe op le in ou r
c o mm u n i ty. So wit h th at sa id
, I—I th in k I fas hi on ed a se nt en ce th at I h o p e is co ns is te nt wit h ou r—wi th th e gu id el in es , an d al so co ns is te n t wit h t he go al s o f 35 53 (a).

(Em ph as es ad de d.)

The di st ric t co ur t s ta te d i t re se arch ed an d ex am in ed BZP ta ki ng in to acco un t th e dr ug 's m

ul ti pl e de le te rio us effe ct s on it s us ers an d th e co m m un it y as co m

pa red to
ot he r dr ug s lis te d in th e Gui de li ne s. W e co nc lu de th at th e d is tri ct co ur t's co m m en ts

m eet "t he req ui rem en t th at th e ch os en se nt en ce be ad eq ua te ly ex pl ai ne d so as to al lo w fo r m e a n i n g f

u l ap pe ll at e rev ie w an d to pr om ot e th e pe rcep ti on of fai r se nt en ci ng ."
Uni te d S ta te s v. Bu rn s , 57 7 F .3d 88 7, 89 2 (8 th Cir . 20 09 ). Acco rd in gl y , th e d is tri ct

co ur t co m

m it te d n o s ig ni fic an t p ro ced ur al erro r in ex pl ai ni ng it s d eci si on to eq ua te BZP wit h M DMA fo r dr ug -q ua nt it y pu rp os es

.

-7

-III. Co nc lu si on

Bas ed on th e fo reg oi ng , we affi rm

.

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-8

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